In an era characterized by an abundance of information, high speed and rapid data consumption, but also by constantly evolving technological development, communication channels and new tools enable leading brands in today’s telecommunication business scene to reshape their communication strategy and use constantly new ways to promote them, achieve their purpose, and reach their consumers and stakeholders. All the above, combined with the dynamics and capabilities of Artificial Intelligence (AI), highlight the need to “transform” brands themselves and their “image” in order to properly listen to new trends and approach consumers in creative and effective ways in the digital environment. The strategic choices and the formation of the communication of leading telecommunication brands and companies operating in Greece in such an environment are the subject of this research. A mixed methodological study was followed. The choice of tools and channels, as well as the overall configuration of strategic communication were approached qualitatively by conducting interviews with executives actively involved in the strategic communication of leading brands and telecommunications companies, as well as by studying and analyzing content. Findings illustrate the evolution of strategic communication in the modern digital environment in the light of leading telecom brands and companies and the penetration of digital tools and Artificial Intelligence (AI) in the design and execution of strategic communication and in defining the target audience for achieving objectives. Implications for the use of AI in strategic communication, the data-driven approach, and the evolution of the strategic communication’ professionals future role are discussed.